EP3060195B1 - Composition cosmétique à base d'acide hyaluronique, procédé de préparation et d'utilisation de celle-ci - Google Patents

Composition cosmétique à base d'acide hyaluronique, procédé de préparation et d'utilisation de celle-ci Download PDF

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Publication number
EP3060195B1
EP3060195B1 EP14816108.6A EP14816108A EP3060195B1 EP 3060195 B1 EP3060195 B1 EP 3060195B1 EP 14816108 A EP14816108 A EP 14816108A EP 3060195 B1 EP3060195 B1 EP 3060195B1
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Prior art keywords
composition according
mol
hyaluronic acid
molecular weight
polyethylene oxide
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EP14816108.6A
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German (de)
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EP3060195A1 (fr
Inventor
Katerina Knotkova
Eva SOUKUPOVA
Jana Ruzickova
Vladimir Velebny
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Contipro AS
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Contipro AS
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0241—Containing particulates characterized by their shape and/or structure
    • A61K8/027—Fibers; Fibrils
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8129—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers or esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers, e.g. polyvinylmethylether
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9794—Liliopsida [monocotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the invention relates to a cosmetic composition based on hyaluronic acid which comprises nanofibres containing hyaluronic acid or a pharmaceutically acceptable salt thereof and at least one carrier polymer, preferably polyethylene oxide, polyvinyl alcohol. Further, it relates to the method of production of the composition which is carried out by means of electrostatic spinning of the mixture in water.
  • Nanofibres are nano materials having a diameter which is usually smaller than 100 nm, Nano glossary. Nanotechnology Task Force, Berlin: Federal Institute for Materials Research and Testing. 24 March 2011. "Taken from ISO/TS 27687:2008 Nanotechnologies - Terminology and definitions for nano-objects - Nanoparticle, nanofibre and nanoplate.”, in most cases, however, the size thereof is within the rasnge of 50 to 800 nm. They may be prepared by various methods. nowadays, perhaps the most frequently used method is the electrostatic spinning method. It is a very simple and effective method for the preparation of ultrathin polymer fibres the diameter of which may vary from approximately 5 to 500 nm, see J.M.Deitzel et al.
  • Nanofibrous materials have unique properties which allow their broad use in many fields. They may find use for example as filters, composite bracings - see e.g. M.M.Bergshoef et al. Adv. Mater. 11 (1999) 1362-1365 , drug carriers - see e.g. E. R. Kenawy et al. J.Control. Release 81 (2002) 57-64 or scaffolds - see e.g. P.Wutticharoenmongkol et al. J. Nanosci. Nanotech. 6(2006)514-522 . Nanofibres are prepared from natural, as well as from synthetic polymers.
  • Frequently used natural polymers include polysaccharides, such as hyaluronic acid, cellulose or chitosan
  • the synthetic ones include polyvinyl alcohol (PVA), polycaprolacton (PCL), polymeric lactic acid (PLA), polyethylene oxide (PEO), acetate cellulose (CA), nylon (NY), or polyurethanes (PU).
  • PVA polyvinyl alcohol
  • PCL polycaprolacton
  • PLA polymeric lactic acid
  • PEO polyethylene oxide
  • CA acetate cellulose
  • NY nylon
  • PU polyurethanes
  • nanomaterials in the form of carriers is common in cosmetics, there are many products on market already, mostly facial creams or serums, containing these materials. More specifically, these are e.g. Revitalift (L'Oreal) which contains Pro-retinol A in the form of nanosoms, then Advanced Night Repair Protective (Estée Lauder) which contains liposoms, Platinéum (Lancians) containing Hydroxyapatit in the form of nanoparticles and the like.
  • Revitalift L'Oreal
  • Advanced Night Repair Protective Estée Lauder
  • Platinéum Lithacil
  • Nanofibres may thus be of use as carriers which help in improving the skin condition and alleviating e.g. indications of ageing thereof.
  • Fathi-Azarbayjani et al. published the preparation of nanofibrous anti-wrinkle facial masks of PVA and cyclodextrins (RM beta-CDs) by the method of electrostatic spinning, which contain vitamins A and C (retinoic and ascorbic acid), nanoparticles of gold and collagen. It is a mask which is in a dry state and therefore the substances linked therein do not undergo hydrolysis.
  • the mask Upon placing the mask on face and moistening thereof, the mask is dissolved within 15 minutes, it releases the active substances and ensures the maximum penetration thereof - see A. Fathi-Azarbayjani et al. AAPS PharmSciTech, 11 (2010) 1164-1170 . In this case, the mask is not deposited on any support backup.
  • the use of nanofibres as carriers of active substances in connection with the possible application in the field of cosmetics was also published in 2013 by Madhaiyan et al. and Sheng et al.
  • the nanofibres were prepared from a biocompatible polymer polycaprolactone (PCL), to which vitamin B 12 was bound - see K.Madhaiyan et al International Journal of Pharmaceutics, 444 (2013) 70-76 .
  • the fibres were prepared from fibroin obtained from silk, to which vitamin E was bound - see X.Sheng et al. International Journal of Biological Macromolecules (2010), doi:10.1016/j.ijbiomac.2013.01.029 .
  • PCL polymer polycaprolactone
  • Polymer substances (acetate cellulose, polyvinyl alcohol, cyclodextrins, polycarpolacton and fibroin), which were used in the above mentioned publications for the preparation of nanofibres are allowed in cosmetics, but, however, they do not belong to the frequently used basic materials. These substances do not have any improving effect on the skin, the presence thereof in the preparations is only additive, they serve first of all for forming the film or for adjusting the viscosity.
  • Korean patent application KR2011110482A describes nanofibres made of hyaluronic acid, containing encapsulated vitamin as a prevention of degradation of the vitamin caused by the sunlight. More specifically, it discloses fibres made of hyaluronic acid containing a vitamin and a water-soluble polymer.
  • the vitamin may be e.g. A or E, the water-soluble polymer is hyaluronic acid.
  • the method of preparation of nanofibres consists in the preparation of a mixture of the vitamin solution and the water-soluble polymer and in electrostatic spinning.
  • the solution of the vitamin is prepared by dissolving the vitamin in ethanol in the presence of a surfactant (such as ceteth and nikkol), the presence of which in the preparation for cosmetic use is undesirable.
  • a surfactant such as ceteth and nikkol
  • the international patent application WO2009045042A discloses the preparation of nanofibres from mixtures of various polymers, including e.g. polyurethane, polyacrylonitril, nylon, polymeric lactic acid, polycarbonate, polycaprolacton and others. Hyaluronic acid was not used in this case. To these fibres, extracts and/or natural essential oils were bound. The possibility of use of said fibres in cosmetics is mentioned.
  • Hyaluronic acid unlike all the above mentioned synthetic polymers, is a substance which is body-innate, it is a part of connective tissues and skin where the main property thereof is to bond water and by this to maintain sufficient hydration. However, with ageing the content thereof in the skin decreases, the hydration is reduced and thereby wrinkles and other signs of ageing occur. That is why hyaluronic acid is added to various cosmetic preparations which are designated for topic, as well as intradermal applications.
  • JP2006182750A discloses the preparation of cosmetics by means of freeze-drying (lyophilisation). It means drying of an aqueous solution containing a mixture of collagen, hyaluronic acid and an ascorbic acid derivative. This mixture is then re-dissolved in water or skin lotion prior to use.
  • Said form of cosmetics is characterized by a long stability and absence of preservatives. Therefore, it is a type of dry cosmetics, however, it is such that it is not formed by nanofibres.
  • the drawback thereof, as compared to the presented nanofibrous cosmetics, is that it's time- and manipulation-demanding and the preparation thereof associated with the lyophilisation is expensive.
  • the step of re-dissolving the lyophilisate extends the time which the customer must spend by the home preparation of the product prior to its application itself.
  • Another Japanese patent application No. JP2004051521A deals with cosmetics comprising a dry cosmetic crude material on a non-woven fibre.
  • the dry crude material may be collagen, vitamin A and C, or hyaluronic acid.
  • the product contains a thickening agent which may be water-soluble alginate, a cellulose derivative, chitosan, chitin, PVA and PVP.
  • the fibre is made of non-woven silk which is filled with natural silk.
  • US patent application No.2010/254961 mentions very low content of HA 0,01 wt.% in nanofibers used for cosmetic purposes wherein HA acts as a humectant.
  • US patent application No.2010/216211 relates to fibrous mats comprising chitosan nanofibers substantionally free of fibers of PEO or PVA. Moreover chitosan is substantionally insoluble in water.
  • the drawbacks resulting from the state-of-the-art solutions are overcome by the cosmetic composition as defined in Claim 1.
  • the cosmetic composition based on hyaluronic acid includes nanofibres comprising at least 1 wt.% of hyaluronic acid or a pharmaceutically acceptable salt thereof and at least one carrier polymer.
  • the advantage of the cosmetic composition is a high content of hyaluronic acid in nanofibres, i.e. up to 90 wt.% or even up to 99 wt.%.
  • hyaluronic acid or a salt thereof is more natural for the skin than other commonly used polymers for the preparation of nanofibres and, as opposed to them, it has a significant positive effect on the skin.
  • the increased concentration thereof smoothes out wrinkles.
  • the HA concentration is up to 24 times lower when applied, and in commercially available facial serums in liquid form the HA concentration is up to 13 times lower when applied, than when using the dry composition according to the invention.
  • nanofibrous products can contain any cosmetic active component, not only vitamins or inorganic particles.
  • the pharmaceutically acceptable salt is selected from the group including any of alkali metal ions, preferably Na + , K + .
  • the carrier polymer is selected from the group containing polyethylene oxide, polyvinyl alcohol, preferably polyethylene oxide.
  • the carrier polymers according to the invention enable to carry out the spinning just in water, without the presence of other polar solvents the presence of which in nanofibres could irritate or dehydrate the skin upon the application of the agent.
  • the nanofibres comprised in the composition according to the invention have a diameter within the range of 1 to 400 nm, preferably 20 to 300 nm, more preferably 50 to 200 nm.
  • the nanofibres included in the composition further comprise a cosmetically active substance.
  • a cosmetically active substance that can be any water-soluble or insoluble substances of various chemical composition and origin which are designated for use in cosmetics.
  • the cosmetically active substance according to the invention is selected from the group including
  • the nanofibres of the composition according to the invention may contain an adjuvant, preferably carboxymethyl cellulose.
  • Another component of the nanofibrous composition according to the invention may be a lipophilic substance in the form of micelles.
  • the water-insoluble substances are spun either in the form of a suspension or polymeric micelles, where the hydrophobic substance is encapsulated in a water-soluble polymer.
  • the lipophilic substance is preferably selected from the group comprising a resin extract from the tree Commiphora Mukul, an extract from Lavadula Stoechas in triglycerides of octanoic acid and decanoic acid, coenzyme Q10, ascorbic acid palmitate, pyridoxine dipalmitate, tocopheryl acetate, glycyrrhetinoic acid, cholesterol.
  • Another preferred embodiment of the invention is a composition including nanofibres containing hyaluronic acid or salts thereof and polyethylene oxide, wherein the weight ratio of hyaluronic acid or the salt thereof with respect to polyethylene oxide is 1/99 to 99/1, preferably 1/99 to 90/10, more preferably 5/95 to 85/15, most preferably 50/50 to 80/20.
  • Another preferred embodiment of the invention is a composition including nanofibres containing hyaluronic acid or salts thereof and polyvinyl alcohol, wherein the weight ratio of hyaluronic acid or the salt thereof with respect to polyvinyl alcohol is 2/98 to 50/50, preferably 5/95 to 50/50, more preferably 20/80 to 50/50.
  • the weight ratio of carboxymethyl cellulose, polyethylene oxide and polyvinyl alcohol in the mixture is from 1/1/0.01 to 1/1/1, preferably 1/1/0.5.
  • the molecular weight of hyaluronic acid or a pharmaceutically acceptable salt thereof contained in the nanofibres included in the composition is within the range of 1x10 4 to 3 x 10 5 g/mol, preferably 5x10 4 to 1.5 x 10 5 g/mol, wherein their content in the dry matter of the nanofibres is preferably at least 1 wt.%, more preferably at least 4.4 wt.% and most preferably at least 50 %.
  • the content of hyaluronic acid or a pharmaceutically acceptable salt thereof is within the range of 2 to 90 %wt., preferably 4.4 to 80 %wt., more preferably 50 to 80 %wt.
  • the molecular weight of the carrier polymer contained in the nanofibres included in the composition according to the invention is within the range from 1 x10 4 to 9x10 5 g/mol, wherein the molecular weight is preferably for polyethylene oxide within the range of 3 x 10 5 to 9 x 10 5 g/mol or for polyvinyl alcohol within the range of 1 x 10 4 to 4 x 10 5 g/mol.
  • the content of the carrier polymer in the dry matter of the nanofibres included in the composition which contains nanofibres comprising hyaluronic acid or a pharmaceuticallly acceptable salt thereof and a mixture of polyethylene oxide, polyvinyl alcohol and carboxymethyl cellulose according to the invention is within the range of 0.001 to 90 %wt., preferably 5 to 65 %wt., wherein the content is preferably for polyethylene oxide within the range of 5 to 90 %wt., preferably 10 to 50 %wt. or for polyvinyl alcohol within the range of 0.001 to 30 %wt., preferably 5 to 25 %wt..
  • the molecular weight of carboxymethyl cellulose contained in the nanofibres included in the composition according to the invention is within the range of 1 x 10 5 to 4 x 10 5 g/mol, preferably 1.5 x 10 5 to 3 x 10 5 g/mol, wherein the content thereof is within the range of 0.001 to 50 %wt., preferably 10 to 40 %wt.
  • the content of the cosmetically active substances in the dry matter of the nanofibres included in the composition according to the invention is within the range of 0.001 to 50 %wt., wherein preferably for the water-soluble peptides it is within the range of 0.001 to 10 %wt. or for the water-soluble polysaccharides it is within the range of 0.005 to 0,5 %wt. or for the water-soluble plant extracts it is within the range of 0.01 to 10 %wt. or for the water-soluble polyols it is within the range of 0.1 to 45 %wt. or for the water-soluble vitamins it is within the range of 0.1 to 5 %wt.
  • composition according to the invention is in the form of a layer, either as a self supporting layer or it is deposited on a support.
  • the composition according to the invention is used as a facial mask.
  • the composition according to the invention is used as a facial serum or a facial cream and it may also be used as a self supporting facial mask.
  • the composition according to the invention is in a water-soluble dry form.
  • the areal weight of a layer of the composition according to the invention for use in cosmetics on a support is within the range of 0.2 to 50 g/m 2 , preferably 1.5 to 20 g/m 2 , more preferably 1.0 to 20 g/m 2 , most preferably 1.3 to 1.7 g/m 2 or 1.7 g/m 2 .
  • the areal weight of a layer of the self-supporting composition according to the invention is within the range of 2 to 50 g/m 2 , preferably 4 to 20 g/m 2 .
  • a layer of the composition according to the invention having a lower areal weight may be used for an every-day care, where the concentration of the substances is only replenished.
  • a layer of the composition according to the invention having a higher areal weight will then be needed, from the cosmetic point of view, for a more intense course.
  • Areal weights of layers of compositions according to this application were determined by means of small samples - standard: ⁇ SN EN 12127 (80 0849).
  • composition according to the invention is deposited on a support
  • the support is meant to be a textile which is preferably selected from the group comprising a woven fabric, warp-knitted fabric, load knitted fabric, non-woven textile or a foil.
  • the material of the textile in the form of a support according to the invention is selected from the group comprising polyester, cellulose, polyurethane, polypropylene, polyethylene, viscose, polyamide or mixtures thereof.
  • the material of the foil in the form of the support according to the invention is selected from the group comprising aluminium, such as an aluminium foil, polyamide, polyester, polypropylene, polyethylene or mixtures thereof.
  • Another embodiment according to the invention is a method of the production of the composition as described above, wherein a spinning solution is prepared, comprising hyaluronic acid, a salt thereof and at least one carrier polymer in water, thereafter it is spun electrostatically.
  • a part of the spinning solution may be an optional addition of a cosmetically active substance and/or an adjuvant, as described above.
  • Another preferred embodiment of the method according to the invention is that micelles containing a lipophilic substance or a mixture thereof, as described above, are added to the spinning solution.
  • the spinning may as well be carried out from a suspension which is formed after the addition of the lipophilic substance or the mixture thereof into the spinning solution.
  • the components of the spinning solution are homogenized in water for 10 to 16 hours, preferably for up to 12 hours.
  • a spinning solution comprising hyaluronic acid or a salt thereof and polyethylene oxide or comprising hyaluronic acid and a mixture of polyethylene oxide, carboxymethyl cellulose and polyvinyl alcohol, wherein it forms 2 to 12 %wt., preferably 4 to 10 %wt., of the spinning solution.
  • the method of preparation of the composition according to the invention allows using hyaluronic acid in a broad scale of molecular weights and in a high concentration and at the same time it allows for a great variability of the concentrations of the individual cosmetic crude materials.
  • the method of production according to the invention proceeds at a temperature falling within the range of 18 to 45 °C and normal pressure from an aqueous medium in electrostatic field, where a bundle of fibres collected on a collector covered with a support, i.e. a textile or a foil, is drawn out of the spinning solution by means of an electrostatic force.
  • a support i.e. a textile or a foil
  • compositions prepared in this way are suitable for topical use in cosmetics.
  • the fibres deposited on the carrier support represent dry facial masks
  • the self-supporting composition according to the invention then represents a dry form of a facial serum, but at the same time it may be used, like the composition deposited on a support, as dry facial masks.
  • the advantage of the composition according to the invention is its dry form, which allows omitting any preservatives, and at the same time the stability of the product is ensured.
  • Other advantages also include the absence of emulsifiers. After the application, no greasy film is left on the skin.
  • the advantage is also the immediate solubility of the composition when in contact with water. It is not necessary to dissolve or to treat in any other way the product prior to its application on the skin.
  • the method of application of the dry composition according to the invention on a support as a facial mask includes several steps: moistening the face, placing the product on the moistened skin for 5-30 minutes, wherein 10 minutes are preferred, then removing the support material from the skin and washing the dry film of the mask by means of water. It is recommended to apply a regular cream after the application.
  • the method of application of the dry composition according to the invention without the support as a facial mask includes the following steps: moistening the face by water by means of a diffuser, optionally by means of sponges; taking the product out of the wrapping by means of tweezers or fingers; applying the product on the skin and spreading the product all over the face and neck.
  • the mask is let to interact for 5 - 20 minutes, then the dry film of the mask is washed by means of water. It is recommended to apply a regular cream after the application.
  • the method of application of the dry composition according to the invention without the support as a facial serum includes these steps: moistening the face by water, optimally by means of a diffuser, taking the product out of the wrapping by means of tweezers, applying the product on the skin and spreading the product all over the face, neck and optionally the neck line.
  • the product remains on the skin, it is not washed off. However, it is necessary to use a sufficient amount of water and spred it thoroughly, so that no visible film remains on the skin.
  • layer means a layer of the composition according to the invention which is formed on the collecting electrode after the spinning of the polymeric mixture.
  • foil usually means a very thin sheet, produced industrially from synthetic polymers and metals.
  • sh-hexapeptide-1 means a peptide the sequence of which contains 6 amino acids. Said sequence is as follows - H-GSPAGS-OH (glycine - serine - proline - alanine - glycine - serine).
  • carrier polymer means a biocompatible naturalor synthetic polymer which may be spun by itself electrostatically, is suitable for cosmetic applications and does not cause any undesirable or systemic toxicity.
  • water-soluble peptides means oligopeptides containing up to 10 amino acids or polypeptides with up to 100 amino acids which are soluble in water.
  • water-soluble proteins means high-molecular biopolymers containing more than 100 amino acids or having the molecular weight within the range of 200 to 180 000 g/mol, which are soluble in water.
  • water-soluble polysaccharides means polymeric saccharides having the molecular weight within the range of 200 000 - 1 500 000 g/mol, which are soluble in water.
  • water-soluble plant extracts means alcoholic extracts from plants or their parts which are suitable for cosmetic applications, do not cause any undesirable or systemic toxicity and which are soluble in water.
  • water-soluble polyols means multiple-hydric alcohols, preferably diols, which are soluble in water.
  • water-soluble vitamins means vitamins of the group B, i.e. B1, B2, B3, B5, B6, H (B7), B9, B12 or vitamin C, or esteric derivatives thereof.
  • the nanofibrous instant cosmetics was prepared on an apparatus 4Spin 4SPIN® C4S LAB, generally with the distance of electrodes of 20 cm and dosage 150 ⁇ l/min. The voltage was within the range of 20 - 60 kV.
  • the images from the scanning electron microscope were made on the apparatus Tescan VEGA II LSU with a tungsten cathode and the maximum resolution of 3 nm.
  • the images were made in the high vacuum regime.
  • the accelerating voltage was 5 kV.
  • NMR spectra of the additives were measured on BRUKER AVANCE 500 (500 MHz) in deuterated water.
  • software of the company Bruker TOPSPIN 1.2 and software 25 SpinWorks 3.1 were used.
  • the qualitative and quantitative determination of the peptides as active substances was performed by means of LC Waters Acquity equipped with a mass spectrometer MALDI-SYNAPT Q-TOF.
  • UV-Vis spectra were measured on a UV-Vis spectrophotometer Varian Cary 100 Cone within the wavelength range of 800 - 190 nm, optionally 400 - 190 nm.
  • Table 1 Examples of active substances and recommended amount thereof Active substance Recommended range of concentrations in the composition whey protein 0.5 % acetyl hexapeptide-8, 3 - 10 % (1%)extract from the above-ground parts (blossoms, leaves, stem) of the plant Epilobium Angustifolium, butyleneglycol 0.1 - 2 % 1% Extract from green seeds of Coffea Arabica , butyleneglycol 0.1 - 2 % - propyleneglycol, extract from the leaves of Cammelia Sinensis 1 - 10 % propyleneglycol, extract from the root of Panax Ginseng 1 - 10 % butyleneglycol 1-10 % glycerol 2 - 5 % propanediol 1
  • HA hyaluronic acid
  • polyethylene oxide having the molecular weight of 400 000 g/mol
  • 0.024 g of whey protein and 75.2 g of water was prepared.
  • the solution was homogenized for 14 hours at the temperature of 20 °C.
  • the solution was spun on a collecting electrode without any support textile.
  • Fig. 1 shows a photo from the scanning electrone microscope.
  • the areal weight of the nanofibrous layer is 11.023 g/m 2 .
  • the diameter of the fibres is 105 nm.
  • HA hyaluronic acid
  • polyethylene oxide having the molecular weight of 400 000 g/mol
  • 94 g of water was prepared.
  • Hyaluronic acid formed 2 % of the dry matter.
  • the solution was homogenized for 10 hours at the temperature of 45 °C.
  • the solution was spun on a collecting electrode without any support textile.
  • the areal weight of the nanofibrous layer is 15.59 g/m 2 .
  • the diameter of the fibres is 144 nm.
  • a solution of 5.88 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol, 0.06 g of polyethylene oxide having the molecular weight of 400 000 g/mol, 0.06 g of polyethylene oxide having the molecular weight of 4 000 000 g/mol and 94 g of water was prepared.
  • Hyaluronic acid formed 98 % of the dry matter.
  • the solution was homogenized for 12 hours at the temperature of 18 °C.
  • the solution was spun on a collecting electrode without any support textile.
  • the areal weight of the nanofibrous layer is 12.3 g/m 2 .
  • the diameter of the fibres is 179 nm.
  • HA hyaluronic acid
  • polyethylene oxide having the molecular weight of 400 000 g/mol
  • 94 g of water was prepared.
  • Hyaluronic acid formed 80 % of the dry matter.
  • the solution was homogenized for 16 hours at the temperature of 20 °C.
  • the solution was spun on a collecting electrode without any support textile.
  • the areal weight of the nanofibrous layer is 14.1 g/m 2 .
  • the diameter of the fibres is 116 nm.
  • HA hyaluronan
  • polyethylene oxide having the molecular weight of 100 000 g/mol
  • 0.024 g of whey protein 0.18 g of acetyl hexapeptide-8 and 75.2 g of water
  • Hyaluronic acid formed 75.75 % of the dry matter.
  • the solution was homogenized for 12 hours at the temperature of 23 °C.
  • the solution was spun on a collecting electrode without any support textile.
  • Fig. 2 shows a photo from the scanning electrone microscope.
  • the areal weight of the nanofibrous layer is 10.08 g/m 2 .
  • the diameter of the fibres is 131 nm.
  • HA hyaluronan
  • polyethylene oxide having the molecular weight of 600 000 g/mol
  • 0.018 g of whey protein 0.108 g of acetyl hexapeptide-8
  • 0.6 g of the extract from the above-ground parts of Epilobium Angustifolium 0.6 g of the extract from the green seeds of Coffea arabica
  • 0.006 g of the extract from the green leaves of Camellia sinensis 0.006 g of the extract from the root of Panax Ginseng and 55.2 g of water was prepared.
  • Hyaluronic acid formed 57.15 % of the dry matter.
  • the solution was homogenized for 14 hours at the temperature of 20 °C.
  • the solution was spun on a collecting electrode without any support textile.
  • Fig. 3 shows a photo from the scanning electrone microscope.
  • the areal weight of the nanofibrous layer is 10.8 g/m 2 .
  • the diameter of the fibres is 148 nm.
  • HA hyaluron
  • Hyaluronic acid formed 3.6 % of the dry matter.
  • the solution was homogenized for 16 hours at the temperature of 40 °C.
  • the solution was spun on a collecting electrode without any support textile.
  • Fig. 4 shows a photo from the scanning electrone microscope.
  • the areal weight of the nanofibrous layer is 11.58 g/m 2 .
  • the diameter of the fibres is 88 nm.
  • HA hyaluronic acid
  • polyvinyl alcohol having the molecular weight of 125 000 g/mol
  • 90 g of water was prepared.
  • Hyaluronic acid formed 2 % of the dry matter.
  • the solution was homogenized for 13 hours at the temperature of 25 °C.
  • the solution was spun on a collecting electrode without any support textile.
  • the areal weight of the nanofibrous layer is 7.77 g/m 2 .
  • the diameter of the fibres is 290 nm.
  • HA hyaluronic acid
  • polyvinyl alcohol having the molecular weight of 125 000 g/mol
  • 90 g of water was prepared.
  • Hyaluronic acid formed 50 % of the dry matter.
  • the solution was homogenized for 15 hours at the temperature of 45 °C.
  • the solution was spun on a collecting electrode without any support textile.
  • the areal weight of the nanofibrous layer is 1 g/m 2 .
  • the diameter of the fibres is 180 nm.
  • Example 10 (HA/PEO/CMC/PVA 4.5/38.2/38.2/19.1)
  • Hyaluronic acid formed 4.5 % of the dry matter.
  • the solution was homogenized for 12 hours at the temperature of 25 °C.
  • the solution was spun on a collecting electrode without any support textile.
  • the areal weight of the nanofibrous layer is 11.023 g/m 2 .
  • the diameter of the fibres is 105 nm.
  • a solution of 1.623 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol and 0.213 g of polyethylene oxide having the molecular weight of 400 000 g/mol, 0.103 g of carboxymethyl cellulose having the molecular weight of 250 000 g/mol, 0.998 g of polyvinyl alcohol having the molecular weight of 125 000 g/mol and 48 g of water was prepared.
  • Hyaluronic acid formed 80 % of the dry matter.
  • the solution was homogenized for 10 hours at the temperature of 40 °C.
  • the solution was spun on a collecting electrode with a support textile (spunbund polypropylene 18 g/m 2 ).
  • the areal weight of the nanofibrous layer is 6.23 g/m 2 .
  • the diameter of the fibres is 96 nm.
  • Hyaluronic acid formed 1 % of the dry matter.
  • the solution was homogenized for 15 hours at the temperature of 22 °C.
  • the solution was spun on a collecting electrode with a support textile (spunbund polypropylene 18 g/m 2 ).
  • the areal weight of the nanofibrous layer is 13.82 g/m 2 .
  • the diameter of the fibres is 62 nm.
  • Hyaluronic acid formed 19.6 % of the dry matter.
  • the solution was homogenized for 12 hours at the temperature of 22 °C.
  • the solution was spun on a collecting electrode with a support textile (spunbund polypropylene 18 g/m 2 ).
  • the areal weight of the nanofibrous layer is 7.35 g/m 2 .
  • the diameter of the fibres is 57 nm.
  • a solution of 0.205 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol and 0.613 g of polyethylene oxide having the molecular weight of 400 000 g/mol, 0.609 g of carboxymethyl cellulose having the molecular weight of 250 000 g/mol, 0.598 g of polyvinyl alcohol having the molecular weight of 125 000 g/mol and 48 g of water was prepared.
  • Hyaluronic acid formed 10 % of the dry matter.
  • the solution was homogenized for 14 hours at the temperature of 40 °C.
  • the solution was spun on a collecting electrode with a support textile (spunbund polypropylene 18 g/m 2 ).
  • the areal weight of the nanofibrous layer is 9.09 g/m 2 .
  • the diameter of the fibres is 54 nm.
  • Sample A contains in its composition HA/PEO and the substances from group A - see Table 2 above (see also Fig. 5A ).
  • Sample B contains in its composition HA/PEO and the substances from groups A + B - see Table 2 above (see also Fig. 5B ).
  • Sample C contains in its composition HA/PEO/CMC/PVA and the substances from group A - see Table 2 above (see also Fig. 5C ).
  • Sample D contains in its composition HA/PEO/CMC/PVA and the substances from groups A + B - see Table 2 above (see also Fig. 5D ).
  • Other two samples contained either HA/PEO and the substances from groups A + B + C or substances from groups A + B + C + D - see Table 2 above.
  • Other two samples contained either HA/PEO/CMC/PVA and either the substances from groups A + B + C or substances from groups A + B + C + D - see Table 2 above.
  • Sample A contains in its composition HA/PEO and the substances from group A - see Table 3 above (see also Fig. 6A ).
  • Sample B contains in its composition HA/PEO and the substances from groups A + B - see Table 3 above (see also Fig. 6B ).
  • Sample C contains in its composition HA/PEO/CMC/PVA and the substances from group A - see Table 3 above (see also Fig. 6C ).
  • Sample D contains in its composition HA/PEO/CMC/PVA and the substances from groups A + B - see Table 3 above (see also Fig. 6D ).
  • Other two samples contained either HA/PEO and the substances from groups A + B + C or the substances from the groups A + B + C + D. - see Table 3 above.
  • Other two samples contained either HA/PEO/CMC/PVA and the substances from groups A + B + C or the substances from the groups A + B + C + D - see Table 3 above.
  • Other two samples contained either HA
  • the ratio 80/20 was retained in the mixture HA/PEO, since the percentual contents of all substances were subtracted from the total dry matter and the remaining dry matter was then divided by the ratio 80/20.
  • a similar approach was applied to the product containing two carrier polymers, hyaluronic acid and an additive which was carboxymethyl cellulose, where again the total sum of the percentual contents was subtracted from the total dry matter and the remainder was divided in the ratio HA/PEO/CMC/PVA 4.5/38.2/38.2/19.1. Production rates of these mixtures are presented in Table 3 as production rates C (HA/PEO) and D (HA/PEO/CMC/PVA).
  • HA hyaluronic acid
  • polyethylene oxide having the molecular weight of 400 000 g/mol
  • 0,009 g whey protein having the molecular weight of 400 000 g/mol
  • 0,009 g whey protein having the molecular weight of 400 000 g/mol
  • 0,009 g whey protein having the molecular weight of 400 000 g/mol
  • 0,009 g whey protein having the molecular weight of 400 000 g/mol
  • propylene glycol 0.9 g of propylene glycol
  • 1.8 g of an extract from the above-ground parts of Epilobium angustifolium 0.18 g of Aloe Barbadensis
  • 0.018 g of sodium carboxymethyl beta-glucan and 280 g of water was prepared.
  • Hyaluronic acid formed 73.1 % of the dry matter.
  • the solution was homogenized for 14 hours at the temperature of 20 °C.
  • the solution was spun to various types of support textiles.
  • Table 4 - List of support textiles, chemical compositions and production rates thereof type of the textile composition areal weight (g/m 2 ) diameter of the fibres (nm) non-woven textile made of nanofibres polyamide + polyester 7.2 72 woven fabric in cloth binding cotton 7.8 88 warp-knitted fabric polyamide + elastan (70:30) 9.0 105 foil low-density PE (fine) 6.6 55 warp-knitted fabric polyester 100% 9.6 85 warp-knitted fabric polyamide and elastan (81:19) 3.0 79 non-woven textile - 10 g/m 2 polypropylene 9.6 3.65 foil low-density polyethylene (PE) (rough) 7.2 92 warp-knitted fabric viscose 4.8 96 jersey fabric cellulose 6.0 92 woven textile cellulose 7.2 97 warp-knitted fabric polyamide monofil 5.4 97 non-woven textile - a hydrophobic modification polyester 13.2 115 non-woven textile polyester 1
  • hyaluronan having the molecular weight of 83 200 g/mol and 0.6 g of polyethylene oxide having the molecular weight of 400 000 g/mol, 0.015 g of creatine and 47 g of water was prepared.
  • Hyaluronic acid formed 79.5 % of the dry matter.
  • the solution was agitated in a shaking apparatus for 12 hours at the temperature of 25 °C. Thereafter it was spun. 10 mg of the sample was dissolved in deuterated water and H 1 NMR spectrum was measured ( Fig. 8 ).
  • the nanofibrous layer containing hyaluronic acid, polyethylene oxide and creatine is shown in Fig. 9 .
  • HA hyaluronic acid
  • polyethylene oxide having the molecular weight of 400 000 g/mol
  • 0.06 g of creatine and 47 g of water was prepared.
  • Hyaluronic acid formed 78 % of the dry matter.
  • the solution was agitated in a shaking apparatus for 16 hours at the temperature of 20 °C. Thereafter it was spun. 10 mg of the sample was dissolved in deuterated water and H 1 NMR spectrum was measured ( Fig. 10 ).
  • the nanofibrous layer containing hyaluronic acid, polyethylene oxide and creatine is shown in Fig. 11 .
  • a solution of 0.4 hyaluronic acid having the molecular weight of 10 000 g/mol containing polymeric micelles with pyridoxine palmitate, 0.1 g of polyethylene oxide having the molecular weight of 600 000 g/mol and 4.5 g of water was prepared.
  • Hyaluronic acid formed 80 % of the dry matter.
  • the solution was agitated in a shaking apparatus for 16 hours at the temperature of 25 °C. Thereafter it was spun.
  • the areal weight of the nanofirbous layer is 10.71 g/m 2 .
  • the nanofibrous layer containing micelles with a lipidic component is shown in Fig. 12 .
  • the diameter of the fibres was 308 nm.
  • HA hyaluronic acid
  • polyethylene oxide having the molecular weight of 400 000 g/mol
  • acetyl hexapeptide-8 188 g of water
  • Hyaluronic acid formed 70 % of the dry matter.
  • the solution was agitated in a shaking apparatus for 14 hours at the temperature of 25 °C. Thereafter it was spun.
  • the nanofibrous layer was cut to circles, in which the concentration of acetyl hexapeptide-8 was measured by means of LC-MS. The initial concentration was 0.1 mg/mg of the sample. After spinning the concentration dropped to 0.08 mg/mg of the sample with a relative error of 3 %. This also proved the homogeneity of the spinning process ( Fig. 15 ).
  • the nanofibrous layer is shown in Fig. 16 .
  • HA hyaluronic acid
  • polyethylene oxide having the molecular weight of 400 000 g/mol
  • 0.06 g whey protein having the molecular weight of 400 000 g/mol
  • 0.06 g whey protein having the molecular weight of 400 000 g/mol
  • 0.06 g whey protein having the molecular weight of 400 000 g/mol
  • 0.06 g whey protein having the molecular weight of 400 000 g/mol
  • 0.06 g whey protein having the molecular weight of 400 000 g/mol
  • 0.06 g whey protein having the molecular weight of 400 000 g/mol
  • 0.06 g whey protein having the molecular weight of 400 000 g/mol
  • 0.06 g whey protein having the molecular weight of 400 000 g/mol
  • 0.06 g whey protein having the molecular weight of 400 000 g/mol
  • 0.06 g whey protein having the molecular weight of 400 000
  • the nanofibrous layer is shown in Fig. 17 .
  • the diameter of the fibres was 162 nm.
  • Table 5 Various durations of the spinning process and the resulting weights time (min) areal weight (g/m 2 ) 1 0.2240 3 0.5920 5 0.8667 7 1.2827 10 1.7400 13 2.5640 15 3.0200 20 4.0880 250 46.8225
  • HA hyaluronic acid
  • a solution 2 was prepared of 4.8 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol and 1.2 g of polyethylene oxide having the molecular weight of 400 000 g/mol.
  • the solution was homogenized in a shaking apparatus for 12 hours. Thereafter, it was spun in a self-supporting way.
  • HA hyaluronic acid
  • a cream serum (emulsion of the o/w type) was prepared of 12 g of triglycerides of octanoic acid and decanoic acid, 5 g of the mixture of glyceryl monostearate and PEG 100 stearate, 2 g of the mixture of sodium acrylate, a copolymer of acryloyl dimethyl taurate, isohexadecane and polysorbate 80, 1.2 g of polyethylene oxide, 4.02 g of hyaluronic acid having the molecular weight of 83 200 g/mol, 0.06 g of plankton extract, 0.18 g of acetyl hexapeptide-8, 0.3 g of an extract from the leaves of Camellia Sinensis, 0.06 g of Aloe Barbadensis, 0.8 g of the mixture of benzylalcohol and dehydro acetic acid and 74.38 g of distilled water.
  • HA hyaluronic acid
  • a solution 2 was prepared of 4.8 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol and 1.2 g of polyethylene oxide having the molecular weight of 600 000 g/mol.
  • the solution was homogenized in a shaking apparatus for 12 hours. Thereafter, it was spun in a self-supporting way.
  • HA hyaluronic acid
  • a cream serum (emulsion of the o/w type) was prepared of 12 g of triglycerides of octanoic acid and decanoic acid, 5 g of the mixture of glyceryl monostearate and PEG 100 stearate, 2 g of the mixture of sodium acrylate, a copolymer of acryloyl dimethyl taurate, isohexadecane and polysorbate 80, 1.2 g of polyethylene oxide, 4.02 g of hyaluronic acid having the molecular weight of 83 200 g/mol, 0.06 g of plankton extract, 0.18 g of acetyl hexapeptide-8, 0.3 g of an extract from the leaves of Camellia Sinensis, 0.06 g of Aloe Barbadensis, 0.8 g of the mixture of benzylalcohol and dehydro acetic acid and 74.38 g of distilled water.
  • HA hyaluronic acid
  • a solution 2 was prepared of 4.8 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol and 1.2 g of polyethylene oxide having the molecular weight of 400 000 g/mol.
  • the solution was homogenized in a shaking apparatus for 12 hours. Thereafter, it was spun in a self-supporting way.
  • HA hyaluronic acid
  • a cosmetic preparation (emulsion of the o/w type) was prepared of 12 g of triglycerides of octanoic acid and decanoic acid, 5 g of the mixture of glyceryl monostearate and PEG 100 stearate, 2 g of the mixture of sodium acrylate, a copolymer of acryloyl dimethyl taurate, isohexadecane and polysorbate 80, 1.2 g of polyethylene oxide, 4.02 g of hyaluronic acid having the molecular weight of 83 200 g/mol, 0.06 g of plankton extract, 0.18 g of acetyl hexapeptide-8, 0.3 g of an extract from the leaves of Camellia Sinensis, 0.06 g of Aloe Barbadensis, 0.8 g of the mixture of benzylalcohol and dehydro acetic acid and 74.38 g of distilled water.
  • HA hyaluronic acid
  • a solution 2 was prepared of 4.8 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol and 1.2 g of polyethylene oxide having the molecular weight of 400 000 g/mol.
  • the solution was homogenized in a shaking apparatus for 12 hours. Thereafter, it was spun in a self-supporting way.
  • HA hyaluronic acid
  • a cosmetic preparation (emulsion of the o/w type) was prepared of 12 g of triglycerides of octanoic acid and decanoic acid, 5 g of the mixture of glyceryl monostearate and PEG 100 stearate, 2 g of the mixture of sodium acrylate, a copolymer of acryloyl dimethyl taurate, isohexadecane and polysorbate 80, 1.2 g of polyethylene oxide, 4.02 g of hyaluronic acid having the molecular weight of 83 200 g/mol, 0.06 g of plankton extract, 0.18 g of acetyl hexapeptide-8, 0.3 g of an extract from the leaves of Camellia Sinensis, 0.06 g of Aloe Barbadensis, 0.8 g of the mixture of benzylalcohol and dehydro acetic acid and 74.38 g of distilled water.
  • a solution 1 of 0.176 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol, 1.528 g of polyethylene oxide having the molecular weight of 400 000 g/mol, 0.768 g of polyvinylalcohol and 1.528 g of carboxymethyl cellulose having the molecular weight of 250 000 g/mol was prepared.
  • the solution was homogenized in a shaking apparatus for 12 hours. Thereafter, it was spun on a polypropylene non-woven textile.
  • a solution 2 was prepared of 0.176 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol, 1.528 g of polyethylene oxide having the molecular weight of 400 000 g/mol, 0.768 g of polyvinylalcohol and 1.528 g of carboxymethyl cellulose having the molecular weight of 250 000 g/mol.
  • the solution was homogenized in a shaking apparatus for 12 hours. Thereafter, it was spun in a self-supporting way.
  • a solution 3 was prepared of 4.8 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol and 1.2 g of polyethylene oxide having the molecular weight of 400 000 g/mol.
  • the solution was homogenized in a shaking apparatus for 12 hours. Thereafter, it was spun in a self-supporting way.
  • HA hyaluronic acid
  • a solution 1 of 0.176 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol, 1.528 g of polyethylene oxide having the molecular weight of 400 000 g/mol, 0.768 g of polyvinylalcohol and 1.528 g of carboxymethyl cellulose having the molecular weight of 250 000 g/mol was prepared.
  • the solution was homogenized in a shaking apparatus for 12 hours. Thereafter, it was spun on a polypropylene non-woven textile.
  • a solution 2 was prepared of 0.176 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol, 1.528 g of polyethylene oxide having the molecular weight of 400 000 g/mol, 0.768 g of polyvinylalcohol and 1.528 g of carboxymethyl cellulose having the molecular weight of 250 000 g/mol.
  • the solution was homogenized in a shaking apparatus for 12 hours. Thereafter, it was spun in a self-supporting way.
  • a solution 3 was prepared of 4.8 g of hyaluronic acid (HA) having the molecular weight of 83 200 g/mol and 1.2 g of polyethylene oxide having the molecular weight of 400 000 g/mol.
  • the solution was homogenized in a shaking apparatus for 12 hours. Thereafter, it was spun in a self-supporting way.
  • HA hyaluronic acid
  • the spun samples of the solutions 1, 2 and 3 having the weight of 5 to 10 mg were applied on a forearm in such a way that the sample of the spun solution 1 was laid with the spun layer to the moistened skin for 15 minutes, then the product together with the textile was cleared off by means of water.
  • the samples of the spun solutions 2 and 3 were applied to the skin, dissolved by means of a defined amount of water, spred on the marked area and left on the skin for 10 minutes. Then the samples were cleared off the skin by means of water.
  • the TEWL values were monitored in times 0.5, 1, 2 and 3 hours from the application ( Fig. 24 ). The measurement was performed by means of the probe Tewameter® TM 300.

Claims (34)

  1. Composition cosmétique sous forme de nanofibres caractérisée en ce qu'elle comprend des nanofibres contenant de l'acide hyaluronique ou un de ses sels pharmaceutiquement acceptables dans la gamme de 50 à 90% en poids, ayant un poids moléculaire compris entre 1x104 et 3 x 105 g/mol,
    et au moins un polymère support choisi dans le groupe constitué par l'oxyde de polyéthylène, l'alcool polyvinylique.
  2. La composition selon la revendication 1, caractérisée en ce que le sel pharmaceutiquement acceptable est choisi dans le groupe comprenant l'un quelconque des ions de métal alcalin, de préférence Na+, K+.
  3. La composition selon la revendication 1 ou la revendication 2, caractérisée en ce que le polymère support est de préférence l'oxyde de polyéthylène.
  4. La composition selon l'une quelconque des revendications précédentes 1 à 3, caractérisée en ce que le diamètre des nanofibres est compris entre 1 et 400 nm, de préférence entre 20 et 300 nm, plus préférentiellement entre 50 et 200 nm.
  5. La composition selon l'une quelconque des revendications précédentes 1 à 4, caractérisée en ce que les nanofibres contiennent en outre une substance cosmétiquement active.
  6. La composition selon la revendication 5, caractérisée en ce que la substance cosmétiquement active est choisie dans le groupe comprenant
    - des peptides hydrosolubles, de préférence choisis dans le groupe comprenant l'acétyl hexapeptide-8, le sh-hexapeptide-1, la protéine de lactosérum ou la protéine de soja,
    - des polysaccharides hydrosolubles, de préférence choisis dans le groupe comprenant le schizophyllan, le carboxyméthylbêta-glucane sodique, le caproylhyaluronate de sodium ou le glucomanane,
    - des extraits végétaux hydrosolubles, de préférence choisis dans le groupe comprenant un extrait des parties aériennes d'Epilobium angustifolium, un extrait de graines vertes de Coffea arabica, un extrait de feuilles de Camellia Sinensis, uns extrait de racines de Panax Ginseng, un extraits d'Aloe Barbadensis, un extrait de plancton,
    - des polyols hydrosolubles, de préférence choisis dans le groupe comprenant le propylène glycol, le butylène glycol, le glycérol;
    - des vitamines hydrosolubles, de préférence choisies dans le groupe comprenant le D-panthénol, ester éthylique de l'acide ascorbique,
    Lactate de micrococcus, créatine, 1-méthylhydantoïne-2-imide, lactate de sodium, glycine, un sel de sodium de l'acide pyroglutamique, fructose, urée, niacinamide, inositol, benzoate de sodium ou acide lactique.
  7. La composition selon l'une quelconque des revendications 1 à 6, caractérisée en ce que les nanofibres contiennent en outre un adjuvant, de préférence la carboxyméthylcellulose.
  8. La composition selon l'une quelconque des revendications 1 à 7, caractérisée en ce que les nanofibres contiennent en outre une substance lipophile sous forme de micelles.
  9. La composition selon la revendication 8, caractérisée en ce que la substance lipophile est de préférence choisie dans le groupe contenant un extrait de résine de l'arbre Commiphora Mukul, un extrait de Lavadula Stoechas dans des triglycérides de l'acide octanoïque et décanoïque, coenzyme Q10, palmitate de l'acide ascorbique, dipalmitate de pyridoxine, acétate de tocophéryle, l'acide glycyrrhétinoïque, cholestérol.
  10. La composition selon l'une quelconque des revendications 1 à 9 caractérisée en ce qu'elle comprend des nanofibres contenant de l'acide hyaluronique ou un sel pharmaceutiquement acceptable de celui-ci et un mélange d'oxyde de polyéthylène, d'alcool polyvinylique et de carboxyméthylcellulose.
  11. La composition selon la revendication 10 caractérisée en ce que le rapport en poids de la carboxyméthylcellulose, de l'oxyde de polyéthylène et de l'alcool polyvinylique dans le mélange est compris entre 1/1 / 0,01 et 1/1/1, de préférence 1/1 / 0,5.
  12. La composition selon l'une quelconque des revendications précédentes 1 à 11, caractérisée en ce que le poids moléculaire de l'acide hyaluronique ou de son sel pharmaceutiquement acceptable est compris dans l'intervalle de 5 x 104 à 1,5 x 105 g / mol.
  13. La composition selon l'une quelconque des revendications précédentes 1 à 12, caractérisée en ce que la masse moléculaire du polymère support est comprise entre 1 x 104 et 9 x 105 g / mol, la masse moléculaire étant de préférence pour l'oxyde de polyéthylène dans l'intervalle 3 x 105 à 9 x 105 g / mol ou pour l'alcool polyvinylique dans l'intervalle de 1 x 104 à 4 x 105 g / mol.
  14. La composition selon la revendication 10 caractérisée en ce que la teneur en oxyde de polyéthylène est comprise entre 10 et 50% en poids. et pour l'alcool polyvinylique, de 5 à 25% en poids.
  15. La composition selon l'une quelconque des revendications précédentes 7 à 14 caractérisée en ce que le poids moléculaire de la carboxyméthylcellulose est compris entre 1 x 105 et 4 x 105 g / mol, de préférence 1,5 x 105 až 3 x 105 g / mol.
  16. La composition selon la revendication 15 caractérisée en ce que la teneur en carboxyméthylcellulose dans la matière sèche des nanofibres est comprise entre 0,001 et 50% en poids, de préférence entre 10 et 40% en poids.
  17. La composition selon l'une quelconque des revendications précédentes 1 à 16, caractérisée en ce qu'elle se présente sous la forme d'une couche, dans laquelle le poids surfacique de la couche est compris entre 1 et 50 g/m2, de préférence entre 4 et 20 g/m2.
  18. La composition selon l'une quelconque des revendications précédentes 1 à 17 caractérisée en ce qu'elle est sous une forme sèche soluble dans l'eau.
  19. La composition selon l'une quelconque des revendications précédentes 17 ou 18, caractérisée en ce que la couche repose sur un support.
  20. La composition selon la revendication 19, caractérisée en ce que le poids surfacique de la couche est de 0,2 à 50 g/m2, de préférence de 1,5 à 20 g/m2.
  21. La composition selon la revendication 19 ou la revendication 20, caractérisée en ce que le support est un textile ou une feuille.
  22. La composition selon la revendication 21, caractérisée en ce que le textile est choisi dans le groupe comprenant tissu tissée, tissu tricoté à chaîne, tissu tricoté chargé, textile non tissé.
  23. La composition selon la revendication 21 ou la revendication 22, caractérisée en ce que le matériau du textile est choisi dans le groupe comprenant le polyester, la cellulose, le polyuréthane, le polypropylène, le polyéthylène, la viscose, le polyamide ou leurs mélanges.
  24. La composition selon la revendication 21, caractérisée en ce que le matériau de la feuille est choisi dans le groupe comprenant l'aluminium, le polyamide, le polyester, le polypropylène, le polyéthylène ou leurs mélanges.
  25. Procédé de production de la composition définie dans l'une quelconque des revendications 1 à 18, caractérisé en ce qu'on prépare une solution de filage contenant de l'acide hyaluronique ou un sel de celui-ci et au moins un polymère support dans l'eau, puis on le file électrostatiquement.
  26. Le procédé selon la revendication 25, caractérisé en ce qu'une substance cosmétiquement active telle que définie dans la revendication 6 est ajoutée à la solution de filage.
  27. Le procédé selon la revendication 25 ou la revendication 26, caractérisé en ce qu'un adjuvant tel que défini dans la revendication 7 est ajouté à la solution de filage.
  28. Le procédé selon l'une quelconque des revendications précédentes 25 à 27, caractérisé en ce que des micelles contenant une substance lipophile ou des mélanges de celles-ci, ou une substance lipophile seule ou leurs mélanges, tels que définis dans la revendication 8, sont ajoutées à la solution de filage.
  29. Le procédé selon l'une quelconque des revendications 25 à 28, caractérisé en ce qu'on utilise une solution de filage contenant de l'acide hyaluronique ou un sel de ce-ci et de l'oxyde de polyéthylène ou contenant de l'acide hyaluronique et un mélange de l'oxyde de polyéthylène, carboxyméthylcellulose et alcool polyvinylique.
  30. Le procédé selon la revendication 29, caractérisé en ce que l'acide hyaluronique avec l'oxyde de polyéthylène ou avec le mélange de polymères l'oxyde de polyéthylène, carboxyméthylcellulose et alcool polyvinylique forment de 2 à 12% en poids, de préférence de 4 à 10% en poids. de la solution de filage.
  31. Le procédé de production de la composition selon les revendications 19 à 24, caractérisé en ce que la composition est appliquée sur un support tel que défini dans les revendications 21 à 24.
  32. Utilisation de la composition selon l'une quelconque des revendications précédentes 1 à 24 en cosmétique.
  33. Utilisation de la composition selon l'une quelconque des revendications 1 à 18 pour la production d'un masque facial, d'une crème pour le visage, d'un sérum facial.
  34. Utilisation de la composition selon l'une quelconque des revendications 19 à 24 pour la production d'un masque facial.
EP14816108.6A 2013-10-25 2014-10-24 Composition cosmétique à base d'acide hyaluronique, procédé de préparation et d'utilisation de celle-ci Revoked EP3060195B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL14816108T PL3060195T3 (pl) 2013-10-25 2014-10-24 Kompozycja kosmetyczna na bazie kwasu hialuronowego, sposób jej wytwarzania oraz jej zastosowanie

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CZ2013-820A CZ308492B6 (cs) 2013-10-25 2013-10-25 Kosmetická kompozice na bázi kyseliny hyaluronové, způsob její přípravy a použití
PCT/CZ2014/000120 WO2015058734A1 (fr) 2013-10-25 2014-10-24 Composition cosmétique à base d'acide hyaluronique, procédé de préparation et d'utilisation de celle-ci

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EP3060195B1 true EP3060195B1 (fr) 2018-09-26

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BR (1) BR112016009071B1 (fr)
CZ (1) CZ308492B6 (fr)
DK (1) DK3060195T3 (fr)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT202100002891A1 (it) * 2021-02-10 2022-08-10 Saati Spa Composizioni polimeriche per la realizzazione di membrane nanofibrose per applicazioni cosmetico-medicali e procedimento per la loro realizzazione

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9687439B1 (en) * 2016-01-21 2017-06-27 Elc Management Llc Methods and compositions for treating aged skin
CN105832600A (zh) * 2016-04-07 2016-08-10 景东旭 余甘子补水美白面膜贴
CN105997657A (zh) * 2016-06-21 2016-10-12 安徽诚亚生物科技有限公司 一种保湿美白中药组合物
ES2887977T3 (es) 2017-01-23 2021-12-29 Afyx Therapeutics As Método para la fabricación de un producto de dos capas a base de fibras electrohiladas
MX2019008155A (es) * 2017-01-23 2019-11-07 Afyx Therapeutics As Metodo para preparar fibras electrohiladas con un alto contenido de una sustancia bioadhesiva.
JP6951111B2 (ja) * 2017-04-24 2021-10-20 第一工業製薬株式会社 ナノファイバー及びそれを用いたフィルタ、並びにそれらの製造方法
CN110785161B (zh) 2017-06-23 2023-06-20 宝洁公司 用于改善皮肤外观的组合物和方法
CN107875090A (zh) * 2017-11-22 2018-04-06 苏州祖原堂纳米科技有限公司 一种含肽修护面膜
KR102566764B1 (ko) * 2018-02-14 2023-08-11 주식회사 엘지화학 보습용 조성물, 마스크 팩, 화장품 및 이의 제조방법
WO2020010036A1 (fr) 2018-07-03 2020-01-09 The Procter & Gamble Company Méthode de traitement d'une affection cutanée
WO2020114530A1 (fr) * 2018-12-03 2020-06-11 Contipro A.S. Kit contenant une préparation biologiquement active
RU2715231C1 (ru) * 2019-10-14 2020-02-26 Сергей Николаевич Таргонский Косметическая маска-пленка для ухода за кожей лица с витаминами в липосомах
IT202000002827A1 (it) 2020-02-13 2021-08-13 Bakel S R L Composizione da elettrofilare
WO2021161252A1 (fr) 2020-02-13 2021-08-19 Bakel S.R.L. Procédé d'électrofilage de polymères naturels
JP2023513740A (ja) 2020-02-13 2023-04-03 バケル エス．アール．エル． エレクトロスピニングされるポリマーをベースとした天然組成物、およびその作製方法
IT202000002833A1 (it) 2020-02-13 2021-08-13 Bakel S R L Procedimento di elettrofilatura
CZ2020207A3 (cs) * 2020-04-09 2021-06-02 Contipro A.S. Pentapeptid odvozený od kaseinu a kompozice, která jej zahrnuje a jejich topické použití
WO2021247496A1 (fr) 2020-06-01 2021-12-09 The Procter & Gamble Company Méthode d'amélioration de la pénétration d'un composé de vitamine b3 dans la peau
US10959933B1 (en) 2020-06-01 2021-03-30 The Procter & Gamble Company Low pH skin care composition and methods of using the same
CN111759749A (zh) * 2020-06-30 2020-10-13 太仓淼品源材料科技有限公司 一种新型的玻尿酸面膜及其制备方法和使用方法
CN111793854B (zh) * 2020-08-13 2023-03-10 山东华熙海御生物医药有限公司 一种透明质酸纤维材料及其制备方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008128484A2 (fr) 2007-04-24 2008-10-30 Cpn Spol. S.R.O. Préparation de nanofibres à partir de polysaccharides et mélanges de ceux-ci avec un alcool polyvinylique
JP2009041117A (ja) 2007-08-06 2009-02-26 Nisshinbo Ind Inc 多糖類ナノファイバー
WO2009120365A2 (fr) 2008-03-27 2009-10-01 Agigma, Inc. Procédés et compositions pour la délivrance d’agents
US20100018641A1 (en) 2007-06-08 2010-01-28 Kimberly-Clark Worldwide, Inc. Methods of Applying Skin Wellness Agents to a Nonwoven Web Through Electrospinning Nanofibers
US20100254961A1 (en) 2007-09-05 2010-10-07 Taiyokagaku Co., Ltd. Water-soluble electrospun sheet

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2195262C2 (ru) * 1999-08-13 2002-12-27 Государственный научный центр вирусологии и биотехнологии "Вектор" Фармакологическое средство на основе гиалуроновой кислоты, обладающее антимикробным, ранозаживляющим и противовоспалительным действием
JP2004051521A (ja) 2002-07-18 2004-02-19 Katakura Chikkarin Co Ltd 不織布に乾燥化粧品成分を含有した化粧料
BRPI0413086A (pt) * 2003-07-30 2006-10-03 Anteis Sa matriz complexa, utilização da mesma, e processo de preparação de uma matriz biocompatìvel pouco biodegradável
US7235295B2 (en) * 2003-09-10 2007-06-26 Laurencin Cato T Polymeric nanofibers for tissue engineering and drug delivery
US7662332B2 (en) * 2003-10-01 2010-02-16 The Research Foundation Of State University Of New York Electro-blowing technology for fabrication of fibrous articles and its applications of hyaluronan
JP2006182750A (ja) 2004-12-27 2006-07-13 Bio Meito:Kk 凍結乾燥化粧品およびその製造方法
JP2008179629A (ja) * 2006-12-27 2008-08-07 Snt Co 化粧用シート
US9163338B2 (en) * 2007-04-11 2015-10-20 Drexel University Fibrous mats containing chitosan nanofibers
KR100910241B1 (ko) 2007-10-02 2009-07-31 주식회사 에이엠오 식물성 천연 추출물 또는 식물성 천연 정유를 함유하는나노섬유 및 이의 제조방법
CZ303471B6 (cs) * 2007-10-03 2012-10-03 Contipro Biotech S.R.O. Prípravek pro hojení ran a prevenci adheze bandáže na ránu obsahující chitosan-glukan
US20110111012A1 (en) * 2009-11-12 2011-05-12 Hemcon Medical Technologies, Inc. Nanomaterial wound dressing assembly
KR20110110482A (ko) 2010-04-01 2011-10-07 중앙대학교 산학협력단 비타민이 함유된 히알우론산 나노섬유
JP2013049927A (ja) * 2011-08-30 2013-03-14 Shinshu Univ 生体適合性を有するナノ繊維及びその製造方法並びに創傷被覆材
JP5871594B2 (ja) * 2011-12-07 2016-03-01 シンワ株式会社 化粧用シート
KR101454421B1 (ko) * 2012-10-25 2014-11-03 주식회사 아모그린텍 자가 용융형 나노섬유로 구성된 미용시트 및 그 제조방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008128484A2 (fr) 2007-04-24 2008-10-30 Cpn Spol. S.R.O. Préparation de nanofibres à partir de polysaccharides et mélanges de ceux-ci avec un alcool polyvinylique
US20100018641A1 (en) 2007-06-08 2010-01-28 Kimberly-Clark Worldwide, Inc. Methods of Applying Skin Wellness Agents to a Nonwoven Web Through Electrospinning Nanofibers
JP2009041117A (ja) 2007-08-06 2009-02-26 Nisshinbo Ind Inc 多糖類ナノファイバー
US20100254961A1 (en) 2007-09-05 2010-10-07 Taiyokagaku Co., Ltd. Water-soluble electrospun sheet
WO2009120365A2 (fr) 2008-03-27 2009-10-01 Agigma, Inc. Procédés et compositions pour la délivrance d’agents

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
CAZES DR.: "A Question of Molecular Weight", AMERICAN POLYMER STANDARDS CORPORATION, November 2017 (2017-11-01), XP055617184, Retrieved from the Internet <URL:http://www.ampolymer.com/QuestionaofMw.html>
FARWICK, M ET AL.: "Low Molecular Weight Hyaluronic Acid: Its effects on epidermal gene expression and skin ageing", SOFW-JOURNAL, vol. 134, November 2008 (2008-11-01), pages 1 - 6, XP055617182
FARWICK, M. ET AL.: "Fifty-kDa Hyaluronic Acid Upregulates Some Epidermal Genes without Changing TNF-a Expression in Reconstituted Epidermis", vol. 24, no. 4, 11 March 2011 (2011-03-11), pages 210 - 217, XP055211222
LI, JUNXING ET AL.: "Electrospinning of Hyaluronic Acid (HA) and HA/Gelatin Blends", MACROMOLECULAR RAPID COMMUNICATIONS, vol. 27, 29 December 2005 (2005-12-29), pages 114 - 120, XP002516877
PAVICIC, TATJANA ET AL.: "Efficacy of Cream-Based Novel Formulation of Hyaluronic Acid of Different Molecular Weights in Anti-Wrinkle Treatment", JOURNAL OF DRUGS IN DERMATOLOGY: JDD, vol. 10, no. 9, September 2011 (2011-09-01), pages 990, XP008146386
UM, IN CHUL ET AL.: "Electro-Spinning and Electro-Blowing of Hyaluronic Acid", BIOMACROMOLECULES, vol. 5, no. 4, 7 May 2004 (2004-05-07), pages 1428 - 1436, XP002483474
YOUNG, DENICE S, HYALURONIC ACID-BASED NANOFIBERS VIA ELECTROSPINNING, 2 April 2010 (2010-04-02)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT202100002891A1 (it) * 2021-02-10 2022-08-10 Saati Spa Composizioni polimeriche per la realizzazione di membrane nanofibrose per applicazioni cosmetico-medicali e procedimento per la loro realizzazione

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ES2699879T3 (es) 2019-02-13
HUE041924T2 (hu) 2019-06-28
RU2016141121A (ru) 2018-04-24
BR112016009071B1 (pt) 2020-07-07
CZ308492B6 (cs) 2020-09-23
BR112016009071A2 (fr) 2017-08-01
BR112016009071A8 (pt) 2018-04-03
CZ2013820A3 (cs) 2015-05-06
RU2016141121A3 (fr) 2018-07-17
RU2679649C2 (ru) 2019-02-12
DK3060195T3 (en) 2019-01-14
JP6783654B2 (ja) 2020-11-11
WO2015058734A1 (fr) 2015-04-30
PL3060195T3 (pl) 2019-03-29
JP2016536305A (ja) 2016-11-24

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